Synthese von 1-Aryl-4-carboxymethyl-2-azetidinonen / Synthesis of 1-Aryl-4-carboxymethyl-2-azetidinones

Abstract
The photochemically induced rearrangement of the 4-diazoacetyl-2-azetidinones 2a-d in wa- ter/acetonitrile leads exclusively to the title compounds 3 a-d provided that certain reaction conditions are fulfilled. This is in contrast to the thermal, silveroxide catalysed Wolff-rearrange- ment of 2a in alcohols which always gives a mixture of 4, 5 and 6. The mechanism of the 1,4-ringopening of 2a to 5 and 6 is discussed.

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